Laboratory of Organic and Macromolecular Chemistry (IOMC) and Jena Center for Soft Matter (JCSM), Friedrich-Schiller-University Jena, Humboldtstr. 10, 07743 Jena, Germany.
Biomacromolecules. 2011 Jul 11;12(7):2591-600. doi: 10.1021/bm2003847. Epub 2011 Jun 8.
A new sugar-substituted 2-oxazoline monomer was prepared using the copper-catalyzed alkyne-azide cycloaddition (CuAAC) reaction. Its copolymerization with 2-ethyl-2-oxazoline as well as 2-(dec-9-enyl)-2-oxazoline, yielding well-defined copolymers with the possibility to tune the properties by thiol-ene "click" reactions, is described. Extensive solubility studies on the corresponding glycocopolymers demonstrated that the lower critical solution temperature behavior and pH-responsiveness of these copolymers can be adjusted in water and phosphate-buffered saline (PBS) depending on the choice of the thiol. By conjugation of 2,3,4,6-tetra-O-acetyl-1-thio-β-d-glucopyranose and subsequent deprotection of the sugar moieties, the hydrophilicity of the copolymer could be increased significantly, allowing a cloud-point tuning in the physiological range. Furthermore, the binding capability of the glycosylated copoly(2-oxazoline) to concanavalin A was investigated.
一种新的糖取代 2-噁唑啉单体是使用铜催化的炔烃-叠氮环加成（CuAAC）反应制备的。描述了其与 2-乙基-2-噁唑啉和 2-（癸-9-烯基）-2-噁唑啉的共聚反应，生成具有明确结构的共聚物，并可通过硫醇-烯“点击”反应来调节其性质。对相应糖基共聚物的广泛溶解性能研究表明，这些共聚物在水中和磷酸盐缓冲盐水（PBS）中的低临界溶液温度行为和 pH 响应性可以根据硫醇的选择进行调节。通过 2,3,4,6-四-O-乙酰基-1-硫-β-d-吡喃葡萄糖的共轭和随后糖部分的脱保护，可以显著提高共聚物的亲水性，允许在生理范围内调整浊点。此外，还研究了糖基化共聚物对刀豆球蛋白 A 的结合能力。
